Experimental Design and Optimization: Application to a Grignard ReactionNaoual Bouzidi and Christel GozziThis 5-week project, which systematically investigates optimizing the synthesis of benzyl-1-cyclopentan-1-ol, constitutes an initiation into research methodology and experimental design to prepare the student-engineer for an industry internship. Other pedagogical goals include experience in synthetic techniques, obtaining reproducible yields, and using quantitative analysis methods.Bouzidi, Naoual; Gozzi, Christel. J. Chem. Educ.2008, 85, 1544.

Addition Reactions |

Alcohols |

Aldehydes / Ketones |

Chemometrics |

Gas Chromatography |

Organometallics |

Synthesis

Saying What You Mean: Teaching Mechanisms in Organic ChemistryJ. Brent FriesenWays to maintain clarity and consistency when teaching reaction mechanisms in organic chemistry include the use of balanced reaction equations, avoiding the use of shortcut notations, including key electrons and bonds in structural representations, and distinguishing between covalent and ionic bonds.Friesen, J. Brent. J. Chem. Educ.2008, 85, 1515.

Learning Theories |

Mechanisms of Reactions |

Reactions

Teaching Reaction Mechanisms Using the Curved Arrow Neglect (CAN) MethodJohn H. Penn and Abdulrahman G. Al-ShammariA new method for teaching organic reaction mechanisms that concentrates on intermediate reaction structures and can be used in a computer-assisted instruction environment is found to significantly enhance student performance in drawing traditional reaction mechanisms.Penn, John H.; Al-Shammari, Abdulrahman G. J. Chem. Educ.2008, 85, 1291.

Data Pooling in a Chemical Kinetics Experiment: The Aquation of a Series of Cobalt(III) ComplexesRichard S. Herrick, Kenneth V. Mills, and Lisa P. NestorDescribes an experiment that introduces students to integrated rate laws, the search for a mechanism that is consistent with chemical and kinetic data, and the concept of activation barriers and their measurement in a curriculum whose pedagogical philosophy makes the laboratory the center of learning for undergraduates in their first two years of instruction.Herrick, Richard S.; Mills, Kenneth V.; Nestor, Lisa P. J. Chem. Educ.2008, 85, 1120.

Coordination Compounds |

Kinetics |

Mechanisms of Reactions |

Rate Law |

UV-Vis Spectroscopy

The Iodochlorination of Styrene: An Experiment That Makes a DifferenceR. Gary Amiet and Sylvia UrbanThis purpose of this laboratory exercise is to determine the various substitution and elimination products generated in the iodochlorination of styrene and their relative proportions through the application of mechanistic principles and a basic knowledge of GCMS and NMR.Amiet, R. Gary; Urban, Sylvia. J. Chem. Educ.2008, 85, 962.

Alkenes |

Constitutional Isomers |

Gas Chromatography |

Instrumental Methods |

Mass Spectrometry |

Mechanisms of Reactions |

NMR Spectroscopy |

Synthesis |

Student-Centered Learning

Evaluating Mechanisms of Dihydroxylation by Thin-Layer ChromatographyBenjamin T. Burlingham and Joseph C. RettigPresents a microscale experiment in which cyclohexene is dihydroxylated under three sets of conditions and the products determined through thin-layer chromatography. Teams of students evaluate proposed mechanisms for each dihydroxylation in light of the data collected.Burlingham, Benjamin T.; Rettig, Joseph C. J. Chem. Educ.2008, 85, 959.

Addition Reactions |

Alkenes |

Diastereomers |

Mechanisms of Reactions |

Microscale Lab |

Stereochemistry |

Synthesis |

Thin Layer Chromatography

Acid-Catalyzed Enolization of β-TetraloneBrahmadeo Dewprashad, Anthony Nesturi, and Joel UrenaThis experiment allows students to use 1H NMR to compare the rates of substitution of benzylic and non-benzylic a hydrogens of -tetralone and correlate their findings with predictions made by resonance theory.Dewprashad, Brahmadeo; Nesturi, Anthony; Urena, Joel. J. Chem. Educ.2008, 85, 829.

Aldehydes / Ketones |

Isotopes |

Mechanisms of Reactions |

NMR Spectroscopy |

Reactive Intermediates |

Resonance Theory |

Synthesis

Organic Synthesis: Strategy and Control (Paul Wyatt and Stuart Warren)Richard PagniOrganic Synthesis is an excellent resource on organic synthesis. Because of the enormous breadth and complexity of the subject, being able to organize the material into coherent units as well as interconnecting them into a coherent whole is key to writing a successful book on organic synthesis. Wyatt and Warren show this skill in abundance.Pagni, Richard. J. Chem. Educ.2008, 85, 785.

Regioselectivity in Organic Synthesis: Preparation of the Bromohydrin of α-MethylstyreneBrad Andersh, Kathryn N. Kilby, Meghan E. Turnis, and Drew L. MurphyIn the described experiment, the regiochemical outcome of the addition of "HOBr" to a-methylstyrene is investigated. Although both "classic" qualitative analysis and instrumental techniques are described, the emphasis of this experiment is on the utilization 13C and DEPT-135 NMR spectroscopy to determine the regiochemical outcome of the addition. Andersh, Brad; Kilby, Kathryn N.; Turnis, Meghan E.; Murphy, Drew L. J. Chem. Educ.2008, 85, 102.

Six Pillars of Organic ChemistryJoseph J. MullinsThis article focuses on a core set of conceptselectronegativity, polar covalent bonding, inductive and steric effects, resonance, and aromaticitythe proper application of which can explain and predict a wide variety of chemical, physical, and biological properties of molecules and conceptually unite important features of general, organic, and biochemistry.Mullins, Joseph J. J. Chem. Educ.2008, 85, 83.

Bioorganic Chemistry |

Covalent Bonding |

Hydrogen Bonding |

Mechanisms of Reactions |

Periodicity / Periodic Table |

Reactive Intermediates |

Resonance Theory

Computational Analysis of Stereospecificity in the Cope RearrangementLaura Glish and Timothy W. HanksExperimental product distributions from the Cope rearrangement of disubstituted 1,5-hexadienes can be readily understood by computer modeling of the various possible transitions states. Visual analysis of these geometries allow students to interpret the computational results by analogy to the familiar chair and boat conformations of substituted cyclohexanes.Glish, Laura; Hanks, Timothy W. J. Chem. Educ.2007, 84, 2001.

Hydration of Acetylene: A 125th AnniversaryDmitry A. Ponomarev and Sergey M. ShevchenkoThe discovery the hydration of alkynes catalyzed by mercury ions by Mikhail Kucherov made possible industrial production of acetaldehyde from acetylene and had a profound effect on the development of industrial chemistry in the 1920th centuries.Ponomarev, Dmitry A.; Shevchenko, Sergey M. J. Chem. Educ.2007, 84, 1725.

Addition Reactions |

Aldehydes / Ketones |

Alkynes |

Catalysis |

Industrial Chemistry |

Reactions

The A1c Blood Test: An Illustration of Principles from General and Organic ChemistryRobert C. KerberThe glycated hemoglobin blood test is a key measure of the effectiveness of glucose control in diabetics. The chemistry of glucose in the bloodstream, which underlies the test and its impact, provides an illustration of the importance of chemical equilibrium and kinetics to a major health problem.Kerber, Robert C. . J. Chem. Educ.2007, 84, 1541.

A Knoevenagel Initiated Annulation Reaction Using Room Temperature or Microwave ConditionsA. Gilbert CookThe product of a Knoevenagel initiated annulation reaction is identified through a guided prelab exercise of the synthesis of the Hagemann ester, and then through the analysis of GCMS, NMR, and IR spectra. The stereochemistry of the product is determined through the NMR spectrum and Karplus curve, and the student is required to write a mechanism for the reaction.Cook, A. Gilbert. J. Chem. Educ.2007, 84, 1477.

Aldehydes / Ketones |

Conformational Analysis |

Gas Chromatography |

IR Spectroscopy |

Mass Spectrometry |

Mechanisms of Reactions |

NMR Spectroscopy |

Stereochemistry |

Synthesis

A Guided-Inquiry Approach to the Sodium Borohydride Reduction and Grignard Reaction of Carbonyl CompoundsRobert E. RosenbergStudents teams identify unknowns and their reaction products and use their data to deduce that esters are less electrophilic than the other carbonyl compounds present, that Grignard reagents are more nucleophilic than sodium borohydride, and that carboxylic acid derivatives do not undergo the nucleophilic addition reactions that are characteristic of aldehydes and ketones. Rosenberg, Robert E. J. Chem. Educ.2007, 84, 1474.

Addition Reactions |

Aldehydes / Ketones |

Esters |

Grignard Reagents |

IR Spectroscopy |

Oxidation / Reduction |

Reactions |

Student-Centered Learning

Control of Chemical Equilibrium by Solvent: A Basis for Teaching Physical Chemistry of SolutionsOleg V. Prezhdo, Colleen F. Craig, Yuriy Fialkov, and Victor V. PrezhdoThe mechanisms by which solvent can be used to control chemical equilibria are analyzed from a thermodynamic perspective and illustrated with several examples. The solvent effect is described in terms of universal- and specific-solvation components, and the practical and pedagogical means of separating these components are discussed.Prezhdo, Oleg V.; Craig, Colleen F.; Fialkov, Yuriy; Prezhdo, Victor V. J. Chem. Educ.2007, 84, 1348.

Equilibrium |

Reactions |

Solutions / Solvents |

Thermodynamics

Reaction-Map of Organic ChemistrySteven MurovThe Reaction-Map of Organic Chemistry has been designed to provide an overview of most of the reactions needed for the organic chemistry course and should help students develop synthetic routes from one functional group to another.Murov, Steven. J. Chem. Educ.2007, 84, 1224.

Addition Reactions |

Electrophilic Substitution |

Elimination Reactions |

Nucleophilic Substitution |

Oxidation / Reduction |

Periodicity / Periodic Table |

Reactions |

Synthesis |

Enrichment / Review Materials

Teaching a Modified Hendrickson, Cram, and Hammond Curriculum in Organic ChemistryJoel M. Karty, Gene Gooch, and B. Gray BowmanDescribes a new organic chemistry curriculum in which fundamental concepts are introduced before mechanisms, and mechanisms are introduced before reactions. Reactions are introduced according to similarities among mechanisms rather than the functional group involved.Karty, Joel M.; Gooch, Gene; Bowman, B. Gray. J. Chem. Educ.2007, 84, 1209.

Markovnikov's RuleRobert C. KerberThe use of Markovniknov and anti-Markovnikov to describe addition reactions and their products has long outlived its utility.Kerber, Robert C. . J. Chem. Educ.2007, 84, 1109.

Addition Reactions |

Reactions |

Mechanisms of Reactions

Markovnikov's RuleRobert C. KerberThe use of Markovniknov and anti-Markovnikov to describe addition reactions and their products has long outlived its utility.Kerber, Robert C. . J. Chem. Educ.2007, 84, 1109.

Addition Reactions |

Reactions |

Mechanisms of Reactions

Oxidation of Aromatic Aldehydes Using OxoneRajani Gandhari, Padma P. Maddukuri, and Thottumkara K. VinodDescribes an eco-friendly procedure for the oxidation of aldehydes to carboxylic acids in water or a water-ethanol mixture using Oxone as the oxidant. The use of eco-friendly solvents, a non-toxic reagent, and the elimination of extraction solvents in the procedure demonstrate important green chemistry themes to students.Gandhari, Rajani; Maddukuri, Padma P.; Vinod, Thottumkara K. J. Chem. Educ.2007, 84, 852.

Aldehydes / Ketones |

Aromatic Compounds |

Aqueous Solution Chemistry |

Carboxylic Acids |

Green Chemistry |

Mechanisms of Reactions |

NMR Spectroscopy |

Oxidation / Reduction

A Green Alternative to Aluminum Chloride Alkylation of XyleneGrigoriy A. Sereda and Vikul B. RajparaPresents a simple laboratory experiment that introduces organic chemistry students to the basic principles of green technologies, such as lack of toxic or bulk byproducts, nontoxicity, and reusability of the catalyst.Sereda, Grigoriy A.; Rajpara, Vikul B. J. Chem. Educ.2007, 84, 692.

Alkylation |

Green Chemistry |

Catalysis |

NMR Spectroscopy |

Reactions |

Synthesis

Effect of a Perturbation on the Chemical Equilibrium: Comparison with Le Châtelier's PrincipleEmilio Martínez TorresThis article develops a general thermodynamic treatment to predict the direction of shift in a chemical equilibrium when it is subjected to a stress. This treatment gives an inequality that relates the change in the perturbed variable and the change that the equilibrium shift produces in the conjugated variable.Torres, Emilio Martínez. J. Chem. Educ.2007, 84, 516.

Equilibrium |

Reactions |

Thermodynamics

The Aldol Addition and Condensation: The Effect of Conditions on Reaction PathwayR. David Crouch, Amie Richardson, Jessica L. Howard, Rebecca L. Harker, and Kathryn H. BarkerDescribes an experiment offering the opportunity for students to observe the critical role that reaction temperature and base strength have in determining the product of the base-mediated addition of a ketone to an aldehyde.Crouch, R. David; Richardson, Amie; Howard, Jessica L.; Harker, Rebecca L.; Barker, Kathryn H. J. Chem. Educ.2007, 84, 475.

Keeping Your Students Awake: Facile Microscale Synthesis of Modafinil, a Modern Anti-Narcoleptic DrugEvangelos Aktoudianakis, Rui Jun Lin, and Andrew P. DicksDescribes the microscale preparation of modafinil, a pharmaceutical recently approved for the treatment of narcolepsy, by a sulfide oxidation reaction. An unusual feature of modafinil is the presence of a chiral sulfoxide functionality where a sulfur atom acts as a stereocenter, demonstrating that atoms other than carbon can act as centers of chirality.Aktoudianakis, Evangelos; Lin, Rui Jun; Dicks, Andrew P. J. Chem. Educ.2006, 83, 1832.

Chirality / Optical Activity |

Drugs / Pharmaceuticals |

Synthesis |

Mechanisms of Reactions |

IR Spectroscopy |

NMR Spectroscopy |

Microscale Lab |

Stereochemistry

Projects That Assist with Content in a Traditional Organic Chemistry CourseJohn J. Esteb, John R. Magers, LuAnne McNulty, and Anne M. WilsonDescribes two projects in organic chemistry, the reaction notebook and the end-of-semester synthesis activity, that are designed to stimulate student ownership of and engagement with course content.Esteb, John J.; Magers, John R.; McNulty, LuAnne; Wilson, Anne M. J. Chem. Educ.2006, 83, 1807.

Developing Critical Thinking Skills: The "Sabotaged" Synthesis of Methyl p-BromobenzoateEric J. Mahan and Mary Alice NadingBefore beginning an experiment, students are told that someone might have sabotaged their experiment to produce other-than-expected results. The objective is to perform the experiment, determine if any sabotage has occurred, and, if so, identify the changes that were made to the reagents as well as the person responsible.Mahan, Eric J.; Nading, Mary Alice. J. Chem. Educ.2006, 83, 1652.

Purification and Modification of Fullerene C60 in the Undergraduate LaboratoryTracey Spencer, Barney Yoo, and Kent KirshenbaumDescribes an experiment for the extraction and column purification of buckminsterfullerene from fullerene-rich soot followed by a one-pot 1,3-dipolar cycloaddition of an azomethine ylide. Characterization of the starting material and product can be performed by UVVis, MS, 1H NMR, and 13C NMR.Spencer, Tracey; Yoo, Barney; Kirshenbaum, Kent. J. Chem. Educ.2006, 83, 1218.

Rapid and Stereoselective Conversion of a trans-Cinnamic Acid to a β-BromostyreneThomas A. EvansThe stereoselective synthesis of an aryl vinyl bromide is accomplished in a rapid microscale reaction of trans-4-methoxycinnamic acid with N-bromosuccinimide in dichloromethane. This guided-inquiry experiment links reactivity, stereochemistry, and mechanism in electrophilic addition reactions of alkenes and in E1 and E2 elimination reactions that form alkenes.Evans, Thomas A. J. Chem. Educ.2006, 83, 1062.

Semiempirical and DFT Investigations of the Dissociation of Alkyl HalidesJack R. WaasEnthalpy changes corresponding to the gas phase heats of dissociation of 12 organic halides were calculated using two semiempirical methods, the HartreeFock method, and two DFT methods. All five methods agreed generally with the expected empirically known trends in the dissociation of alkyl halides.Waas, Jack R. J. Chem. Educ.2006, 83, 1017.

A Greener Approach to Aspirin Synthesis Using Microwave IrradiationIngrid Montes, David Sanabria, Marilyn García,, Joaudimir Castro, and Johanna FajardoPresents an inquiry-based laboratory experience based on the use of a microwave oven as a means for a comparative study of the effect of different catalysts in the synthesis of aspirin. Montes, Ingrid; Sanabria, David; García,, Marilyn; Castro, Joaudimir; Fajardo, Johanna. J. Chem. Educ.2006, 83, 628.

Drugs / Pharmaceuticals |

Esters |

Green Chemistry |

NMR Spectroscopy |

Reactions |

Synthesis |

Thin Layer Chromatography

Ozonolysis Problems That Promote Student ReasoningRay A. Gross Jr.The structural features inherent in acyclic monoterpenes that follow the isoprene rule often lead to unique sets of ozonolysis products from which their structures, excluding stereochemistry, can be determined from molecular formulas only. This article shows how students may elucidate the structures of these compounds by analysis of the oxidative and reductive workup products.Gross, Ray A., Jr. J. Chem. Educ.2006, 83, 604.

Just Click It: Undergraduate Procedures for the Copper(I)-Catalyzed Formation of 1,2,3-Triazoles from Azides and Terminal AcetylenesWilliam D. Sharpless, Peng Wu, Trond Vidar Hansen, and James G. LindbergIn keeping with the defining aspects of click chemistry, this reaction is high-yielding, requires no chromatography, is easily monitored by TLC, and displays distinct peaks in both IR and 1H-NMR. Virtually all products precipitate, and with just a few different starting blocks, every student, or pair of lab partners, can produce a unique "clicked" compound.Sharpless, William D.; Wu, Peng; Hansen, Trond Vidar; Lindberg, James G. J. Chem. Educ.2005, 82, 1833.

Named Organic Reactions, 2nd Edition (Thomas Laue and Andreas Plagens)R. W. HolmanNamed Organic Reactions is a collection of 134 of the most common named organic reactions, with common being defined as those reactions most likely addressed in the combination of a typical sophomore organic chemistry sequence plus an advanced undergraduatebeginning graduate organic reactions and synthesis course. Holman, R. W. J. Chem. Educ.2005, 82, 1780.

Synthesis |

Mechanisms of Reactions

Named Organic Reactions, 2nd Edition (Thomas Laue and Andreas Plagens)R. W. HolmanNamed Organic Reactions is a collection of 134 of the most common named organic reactions, with common being defined as those reactions most likely addressed in the combination of a typical sophomore organic chemistry sequence plus an advanced undergraduatebeginning graduate organic reactions and synthesis course. Holman, R. W. J. Chem. Educ.2005, 82, 1780.

A GC–MS Analysis of an SN2 Reaction for the Organic LaboratoryMalgorzata M. Clennan and Edward L. ClennanThis experiment utilizes an SN2 reaction between an alkyl bromide and potassium acetate to introduce the use of mass spectrometry for structural identification. It also provides students with experience in organic synthesis, the use of IR to identify functional groups, and the use of gas chromatography and response factors to determine product ratios. Clennan, Malgorzata M.; Clennan, Edward L. J. Chem. Educ.2005, 82, 1676.

IR Spectroscopy |

Mass Spectrometry |

Synthesis |

Chromatography |

Esters |

Mechanisms of Reactions |

Microscale Lab |

Gas Chromatography

Laboratory Experiments on the Electrochemical Remediation of the Environment. Part 8. Microscale Simultaneous PhotocatalysisJorge G. Ibanez, Rodrigo Mena-Brito, and Arturo Fregoso-InfanteIn this article we describe a microscale experiment in which the simultaneous oxidation of an organic compound (citric acid) and the reduction of a metal ion (Cu2+) are photocatalytically performed in an aqueous slurry containing TiO2 irradiated with UV light. This produces electrons (capable of reducing the metal ions) and holes (capable of oxidizing the organic molecule) that can be used for environmental clean up. The experiment allows students to have a better comprehension of the different phenomena involved in a typical photocatalytic process. Ibanez, Jorge G.; Mena-Brito, Rodrigo; Fregoso-Infante, Arturo. J. Chem. Educ.2005, 82, 1549.

Aqueous Solution Chemistry |

Electrochemistry |

Microscale Lab |

Oxidation / Reduction |

Reactions |

Photochemistry |

Semiconductors |

UV-Vis Spectroscopy

Laboratory Experiments on the Electrochemical Remediation of the Environment. Part 7: Microscale Production of OzoneJorge G. Ibanez, Rodrigo Mayen-Mondragon, M. T. Moran-Moran, Alejandro Alatorre-Ordaz, Bruce Mattson, and Scot EskestrandOzone, a powerful oxidizing and disinfecting agent, is produced electrochemically in the undergraduate laboratory with simple equipment and under very mild conditions. Tests are given to characterize it, to observe its action in simulated environmental applications, and to measure its rate of production. Ibanez, Jorge G.; Mayen-Mondragon, Rodrigo; Moran-Moran, M. T.; Alatorre-Ordaz, Alejandro; Mattson, Bruce; Eskestrand, Scot. J. Chem. Educ.2005, 82, 1546.

Aqueous Solution Chemistry |

Descriptive Chemistry |

Electrochemistry |

Electrolytic / Galvanic Cells / Potentials |

Laboratory Equipment / Apparatus |

Microscale Lab |

Oxidation / Reduction |

Reactions

"It Gets Me to the Product": How Students Propose Organic MechanismsGautam Bhattacharyya and George M. BodnerBecause practicing organic chemists use the arrow-pushing formalism in situations that are far removed from the simple contexts in which they are first presented, this study probed how students enrolled in a first-semester, graduate-level organic chemistry course approached the task of writing the mechanisms for two- to four-step reactions that lacked the typical cues that bring common mechanisms to mind. This article focuses on the students' solutions and discusses possible limitations of their strategies. Bhattacharyya, Gautam; Bodner, George M. J. Chem. Educ.2005, 82, 1402.

Mechanisms of Reactions |

Learning Theories |

Constructivism

Diels–Alder Synthesis of endo-cis-N-Phenylbicyclo[2.2.2]oct-5-en-2,3-dicarboximideMarsha R. Baar and Kristin Wustholzendo-cis-N-Phenylbicyclo[2.2.2]oct-5-en-2,3-dicarboximide was synthesized by a DielsAlder cycloaddition of 1,3-cyclohexadiene and N-phenylmaleimide in ethyl acetate. 1,3-Cyclohexadiene and N-phenylmaleimide were selected to illustrate the Alder rule, which reflects a preference for endo products and to overcome the difficulties associated with the traditional combination of 1,3-cyclopentadiene and maleic anhydride. Baar, Marsha R.; Wustholz, Kristin. J. Chem. Educ.2005, 82, 1393.

Asymmetric Synthesis |

Microscale Lab |

Stereochemistry |

Addition Reactions |

Alkenes |

IR Spectroscopy |

NMR Spectroscopy

Application of ChemDraw NMR Tool: Correlation of Program-Generated 13C Chemical Shifts and pKa Values of para-Substituted Benzoic AcidsHongyi WangAn application of ChemDraw NMR Tool was demonstrated by correlation of program-generated 13C NMR chemical shifts and pKa values of para-substituted benzoic acids. Experimental 13C NMR chemical shifts were analyzed in the same way for comparison. The project can be used as an assignment at the end of the first-year organic chemistry course to review topics or explore new techniques: Hammett equation, acidbase equilibrium theory, electronic nature of functional groups, inductive and resonance effects, structurereactivity relationship, NMR spectroscopy, literature search, database search, and ChemDraw software.Wang, Hongyi. J. Chem. Educ.2005, 82, 1340.

Acids / Bases |

Equilibrium |

NMR Spectroscopy |

Aqueous Solution Chemistry |

Carboxylic Acids

Using Building-Block Puzzles To Practice Drawing Organic MechanismsEnder ErdikThis pencil-and-paper activity is designed to test the ability of students in writing intermediates and products in the reactions of ketones. An undergraduate student who is successful in organic chemistry at the sophomore level is expected to fill in empty boxes with the appropriate "building blocks", which are atoms and atom groups (neutral or ionic). Solving the puzzle will give the formulas of reactants, reactive intermediates, and products. Students test their understanding of reaction mechanisms while having fun.Erdik, Ender. J. Chem. Educ.2005, 82, 1325.

Reactive Intermediates |

Synthesis |

Aldehydes / Ketones |

Mechanisms of Reactions

Conversion of an Aziridine to an Oxazolidinone Using a Salt and Carbon Dioxide in WaterJustin R. Wallace, Deborah L. Lieberman, Matthew T. Hancock, and Allan R. PinhasAn undergraduate laboratory experiment that allows for optimization of experimental reaction conditions for the conversion of a readily-available aziridine to the corresponding oxazolidinone using only carbon dioxide and a salt in water is discussed. A variety of salts were used to determine their effect on the reaction. In all cases, either no reaction occurred or a high yield of product was obtained. Ring opening of the less substituted carbonnitrogen bond predominates. This experiment allows students to optimize reaction conditions to obtain predominantly one of two regioisomers. Wallace, Justin R.; Lieberman, Deborah L.; Hancock, Matthew T.; Pinhas, Allan R. J. Chem. Educ.2005, 82, 1229.

Heterocycles |

Synthesis |

Aqueous Solution Chemistry |

Constitutional Isomers |

Mechanisms of Reactions |

NMR Spectroscopy |

Quantitative Analysis

Chemistry Comes Alive!, Volume 7Abstract of Special Issue 32, a CD-ROM of Flames and ExplosionsRachel Bain, Jerrold J. Jacobsen, James H. Maynard, and John W. MooreA visual library containing more than 230 QuickTime movies and more than 6700 still images, Chemistry Comes Alive! Volume 7: Flames and Explosions features the kind of chemistry that is sure to spark an interest. Organized using both the periodic table and type of reaction, CCA! 7 makes it easy for you to find the movie or image you seek to add that spark of interest to your presentation. CCA! 7 covers a broad range of spectacular chemical reactions while also offering a depth of coverage that encourages discussions that compare and contrast particular reactions.Bain, Rachel; Jacobsen, Jerrold J.; Maynard, James H.; Moore, John W. J. Chem. Educ.2005, 82, 1102.

Reactions |

Mechanisms of Reactions

Generation, Isolation, and Characterization of a Stable Enol from Grignard Addition to a Bis-Ester. A Microscale Experiment for the Undergraduate Organic Chemistry LaboratoryOlivier J.-C. Nicaise, Kyle F. Ostrom, and Brent J. DalkeA microscale experiment for the undergraduate organic chemistry laboratory that consists of preparing and characterizing an alpha-ketoester and its corresponding, remarkably stable enol form, has been developed. The reaction is that of a Grignard reagent with a bis-ester. A difference in reaction temperature is responsible for the selective generation of the alpha-ketoester and the enol ester. Analysis of spectral data (1H NMR and IR) and a knowledge of organic reactions allows the students to determine the detailed structure of the two reaction products and also to suggest a mechanism for their formation. This experiment introduces students to the concept of stability of the tetrahedral intermediate in acyl-transfer reactions. It also gives them a taste of the unexpected. Nicaise, Olivier J.-C.; Ostrom, Kyle F.; Dalke, Brent J. J. Chem. Educ.2005, 82, 1059.

IR Spectroscopy |

Mechanisms of Reactions |

Microscale Lab |

NMR Spectroscopy |

Organometallics |

Reactive Intermediates |

Synthesis

The Ethylene Ketal Protecting Group Revisited: The Synthesis of 4-Hydroxy-4,4-diphenyl-2-butanoneMarsha R. Baar, Charles E. Russell, and Kristin L. WustholzThe multistep synthesis of 4-hydroxy-4,4-diphenyl-2-butanone from ethyl acetoacetate illustrates the use of a ketal protecting group. Reaction of ethyl acetoacetate with ethylene glycol with p-TsOH in toluene produced the ketal ester. Reaction of the crude ketal ester with two equivalents of phenyl magnesium bromide followed by an aqueous acid workup generated the tertiary alcohol and simultaneously removed the ketal protecting group to produce the hydroxyketone. Our procedure is a modification of a previously published synthesis whose end product was 4,4-diphenyl-3-buten-2-one, the dehydrated analog. Baar, Marsha R.; Russell, Charles E.; Wustholz, Kristin L. J. Chem. Educ.2005, 82, 1057.

Synthesis |

Grignard Reagents |

IR Spectroscopy |

Mechanisms of Reactions |

NMR Spectroscopy

Circular Dichroism Investigation of Dess–Martin Periodinane Oxidation in the Organic Chemistry LaboratoryNicole A. Reed, Robert D. Rapp, Christian S. Hamann, and Pamela G. ArtzUsing circular dichroism, organic laboratory students investigated the change in absolute stereochemistry upon oxidation of menthol to menthone. In the first laboratory period, the oxidation was performed with DessMartin periodinane, which is a facile and less toxic oxidizing agent. Half the laboratory group performed the oxidation with ()-menthol and the other half used (+)-menthol to produce ()-menthone and (+)-menthone, respectively. The products were analyzed in the second laboratory period using infrared spectroscopy and gas chromatography/mass spectrometry to determine the fraction of starting alcohol converted to ketone. Comparison was made between CD spectra both for the menthol reactant and menthone product and for the (+)- and ()-menthone enantiomers.Reed, Nicole A.; Rapp, Robert D.; Hamann, Christian S.; Artz, Pamela G. J. Chem. Educ.2005, 82, 1053.

Instrumental Methods |

Molecular Properties / Structure |

Oxidation / Reduction |

Reactions |

Enantiomers

The Addition of Bromine to 1,2-Diphenylethene Judith C. Amburgey-Peters and LeRoy W. HaynesWe investigated the reaction of (Z)-1,2-diphenylethene (cis-stilbene) with various brominating reagents and solvents following directions in standard organic chemistry manuals. We were particularly interested in learning which combination of brominating reagent and solvent gave the best yield of (d,l)-1,2-dibromo-1,2-diphenylethane without the formation of significant amounts of meso-1,2-dibromo-1,2-diphenylethane, which is essentially the sole product from the reaction of bromine with (E)-1,2-diphenylethene (trans-stilbene). Based on the results from the standard preparatory methods, some permutations of solvent and brominating reagent were tried.Amburgey-Peters, Judith C.; Haynes, LeRoy W. J. Chem. Educ.2005, 82, 1051.

Addition Reactions |

Alkenes |

Carbocations |

Diastereomers |

Enantiomers |

Mechanisms of Reactions |

Stereochemistry

Formation of α-Tetralone by Intramolecular Friedel–Crafts AcylationMichael S. Holden, R. David Crouch, and Kathryn A. BarkerA microscale procedure is described for the formation of the industrially-important compound alpha-tetralone. This is an example of an intramolecular FriedelCrafts acylation, utilizing 4-phenylbutanoic acid and a proton source. The title reaction demonstrates the concept of ring-forming reactions and highlights the use of carboxylic acids as an electrophile precursor in electrophilic aromatic substitution reactions. Holden, Michael S.; Crouch, R. David; Barker, Kathryn A. J. Chem. Educ.2005, 82, 934.

Aromatic Compounds |

Microscale Lab |

Synthesis |

Carboxylic Acids |

IR Spectroscopy |

NMR Spectroscopy

"You're Repulsive!"Teaching VSEPR in a Not-So-Elegant WayRobert S. H. LiuValence shell electron pair repulsive (VSEPR) interaction is an important concept particularly in discussing structural properties of molecules. In this article we showed five organic examples not commonly associated with VSEPR but yet all involving repulsive interactions of valence electrons, which provides ready explanations for altered chemical reactivity and spectroscopic properties of organic compounds. The ready catchy phrase Youre Repulsive! is the common thread used throughout these five examples.Liu, Robert S. H. J. Chem. Educ.2005, 82, 558.

Mechanisms of Reactions |

UV-Vis Spectroscopy |

Reactions |

Addition Reactions |

Electrophilic Substitution

Procedure for Decomposing a Redox Reaction into Half-ReactionsIlie Fishtik and Ladislav H. BerkaThe principle of stoichiometric uniqueness provides a simple algorithm to check whether a simple redox reaction may be uniquely decomposed into half-reactions in a single way. For complex redox reactions the approach permits a complete enumeration of a finite and unique number of ways a redox reaction may be decomposed into half-reactions. Several examples are given. Fishtik, Ilie; Berka, Ladislav H. J. Chem. Educ.2005, 82, 553.

Stoichiometry |

Equilibrium |

Electrochemistry |

Oxidation / Reduction |

Reactions |

Thermodynamics

The Evolution of a Green Chemistry Laboratory Experiment: Greener Brominations of StilbeneLallie C. McKenzie, Lauren M. Huffman, and James E. HutchisonWe describe two new greener alkene bromination reactions that offer enhanced laboratory safety and convey important green chemistry concepts, in addition to illustrating the chemistry of alkenes. The two alternative reactions, one involving pyridinium tribromide and a second using hydrogen peroxide and hydrobromic acid, are compared to the traditional bromination of stilbene through the application of green metrics, including atom economy, percent experimental atom economy, E factor, and effective mass yield.McKenzie, Lallie C.; Huffman, Lauren M.; Hutchison, James E. J. Chem. Educ.2005, 82, 306.

Synthesis |

Green Chemistry |

Aromatic Compounds |

Addition Reactions |

Alkenes

A Substitute for “Bromine in Carbon Tetrachloride”Joshua M. Daley and Robert G. LandoltBenzotrifluoride (BTF) is a suitable solvent substitute for carbon tetrachloride in experiments requiring application of bromine (Br2) in free radical or addition reactions with organic substrates. A 1 M solution of Br2 in BTF may be used to distinguish hydrocarbons based on the ease of abstraction of hydrogen atoms in thermally or light-induced free radical substitutions. Efficacy of minimization of solvent use, by aliquot addition to neat samples, has been established.Daley, Joshua M.; Landolt, Robert G. J. Chem. Educ.2005, 82, 120.

Alkenes |

Free Radicals |

Green Chemistry |

Qualitative Analysis |

Reactions

The Sharpless Asymmetric Dihydroxylation in the Organic Chemistry Majors LaboratoryChristopher J. Nichols and Melissa R. TaylorA six-period laboratory exercise has been developed that uses the convenient Sharpless asymmetric dihydroxylation (AD) to illustrate the principles of a chiral synthesis. Using one particular alkene, students perform a racemic dihydroxylation, an AD using a commercially available AD-mix, and then an AD using an ester derivative of dihydroquinidine that they synthesized themselves. The structures of the products are confirmed with 1H NMR spectroscopy and the enantiomeric excesses of the diols are determined using a chiral GC column. Nichols, Christopher J.; Taylor, Melissa R. J. Chem. Educ.2005, 82, 105.

Chirality / Optical Activity |

Chromatography |

IR Spectroscopy |

NMR Spectroscopy |

Synthesis |

Alkenes |

Addition Reactions

Combinatorial Partial Hydrogenation Reactions of 4-Nitroacetophenone. An Undergraduate Organic LaboratoryKevin W. Kittredge, Susan S. Marine, and Richard T. TaylorA combinatorial organic chemistry experiment that utilizes an inexpensive commercially available parallel reactor, Argonaut's FirstMate, is described. Students perform a metal catalyzed partial hydrogenation reaction on a multi-functionalized substrate and analyze product ratios by GCMS. Students evaluate a simple organic reaction that yields four different products. The reactions are performed in the presence and absence of a reaction modifier, methanesulfonic acid. Differing product ratios are obtained with the different types of metal catalysts and with the presence or the absence of the reaction modifier. Kittredge, Kevin W.; Marine, Susan S.; Taylor, Richard T. J. Chem. Educ.2004, 81, 1494.

Catalysis |

Combinatorial Chemistry |

Synthesis |

Reactions

Solvent-Free Wittig Reaction: A Green Organic Chemistry Laboratory ExperimentSam H. Leung and Stephen A. AngelIn this experiment (E)- and (Z)-1-(4-bromophenyl)-2-phenylethene are synthesized by a solvent-free Wittig reaction. The reaction is effected by grinding the reactants in a mortar with a pestle. Both the E and Z isomers of the product are produced as evidenced by thin-layer chromatography and 1H NMR analysis. The E isomer is isolated by crystallization with ethanol in this experiment. In addition to learning about the Wittig reaction, students are also introduced to the ideas of mechanochemistry and green chemistry.Leung, Sam H.; Angel, Stephen A. J. Chem. Educ.2004, 81, 1492.

The Conversion of Carboxylic Acids to Ketones: A Repeated DiscoveryJohn W. Nicholson and Alan WilsonThis article describes the history of the reaction converting carboxylic acids to ketones. The reaction has been rediscovered several times, yet has actually been known for centuries. Nicholson, John W.; Wilson, Alan. J. Chem. Educ.2004, 81, 1362.

Synthesis |

Carboxylic Acids |

Aldehydes / Ketones

Exploring Organic Mechanistic Puzzles with Molecular ModelingGail Horowitz and Gary SchwartzMolecular modeling projects in the form of mechanistic organic puzzles are described. Students, working in small groups, deduced reaction mechanisms and calculated heats of formation of intermediates and products in order to predict thermodynamic and kinetic selectivities of reaction. Student performance and degree of success is discussed. Projects are appropriate for students who have completed one semester of organic chemistry. A 3 - 4 hour laboratory period is required. Horowitz, Gail; Schwartz, Gary. J. Chem. Educ.2004, 81, 1136.

Keynotes in Organic Chemistry (Andrew F. Parsons)Joel M. KartyAs a result of the trend towards modularization of chemistry courses, the text attempts to meet the need for smaller, highly focused and accessible organic chemistry textbooks, which complement the very detailed standard texts, to guide students through the key principles of the subject.Karty, Joel M. J. Chem. Educ.2004, 81, 651.

Acids / Bases |

Equilibrium |

Mechanisms of Reactions |

Thermodynamics

The Electrophilic Aromatic Substitution of Fluorobenzene Addison AultJoel Rosenthal and David Schuster published a paper entitled The Anomalous Reactivity of Fluorobenzene in Electrophilic Aromatic Substitution and Related Phenomena. The authors and the reviewers, apparently, were not aware of my publication in this Journal in 1966 entitled The Activating Effect of Fluorine in Electrophilic Aromatic Substitution.Ault, Addison. J. Chem. Educ.2004, 81, 644.

Aromatic Compounds |

Mechanisms of Reactions |

Synthesis

The Tragedy of Hamlet, Son of an Organic Chemist of DenmarkRonald G. BrisboisHerein, Hamlet (the son of an organic chemist of Denmark) is the surrogate of any and every student as he uses a thoroughly Shakespearean approach to sorting out some of the key distinguishing features of SN2 versus SN1 reactions. Brisbois, Ronald G. J. Chem. Educ.2004, 81, 502.

Why Chemical Reactions Happen (James Keeler and Peter Wothers)John KrenosBy concentrating on a limited number of model reactions, this book presents chemistry as a cohesive whole by tying together the fundamentals of thermodynamics, chemical kinetics, and quantum chemistry, mainly through the use of molecular orbital interpretations. Krenos, John. J. Chem. Educ.2004, 81, 201.

Reactions (→) vs Equations (=)S. R. LoganA recent chemical kinetics text uses an equals sign for an overall reaction, whereas an arrow is used in each of the reaction steps that are proposed to constitute the mechanism, and for any elementary process. Logan, S. R. J. Chem. Educ.2003, 80, 1258.

Organic Functional Group Playing Card DeckMichael J. WelshOrganic functional group playing card deck used for review of the name and structure of organic functional groups that can be used to play any game that a normal deck of cards is used for.Welsh, Michael J. J. Chem. Educ.2003, 80, 426.

The Application of the Concept of Extent of ReactionAdela E. CroceEffectively applying the concept of extent of reaction and the degree of advancement in describing the course of a chemical reaction (particularly multistep reactions) and expressing reaction rate equations.Croce, Adela E. J. Chem. Educ.2002, 79, 506.

An Idea Whose Time Has Come? (re J. Chem. Educ. 1999, 76, 1718-1722) William B. JensenPast classifications related to the nine-category classification of organic electrophilic-nucleophilic reactions based on the bonding and symmetry characteristics of the reactants' frontier orbitals of the author.Jensen, William B. J. Chem. Educ.2001, 78, 727.

Covalent Bonding |

Mechanisms of Reactions |

MO Theory

An Idea Whose Time Has Come? (re J. Chem. Educ. 1999, 76, 1718-1722) William B. JensenPast classifications related to the nine-category classification of organic electrophilic-nucleophilic reactions based on the bonding and symmetry characteristics of the reactants' frontier orbitals of the author.Jensen, William B. J. Chem. Educ.2001, 78, 727.

Application of Hammond's Postulate. An Activity for Guided Discovery Learning in Organic ChemistryJ. E. Meany, Vicky Minderhout, and Y. PockerIn this activity, students are given product distributions and other relevant experimental data concerning the free radical chlorination and bromination of propane. Students are guided in the use of Hammond's postulate to predict transition-state structures and to provide a rationale for the relationship between selectivity and reactivity in these and other reactions.Meany, J. E.; Minderhout, Vicky; Pocker, Y. J. Chem. Educ.2001, 78, 204.

A Simple Method for Demonstrating Enzyme Kinetics Using Catalase from Beef Liver ExtractKristin A. JohnsonA simple visual method of demonstrating enzyme kinetics using beef liver catalase. Filter paper is saturated with beef liver extract and placed into a solution of hydrogen peroxide. The catalase in the extract decomposes the hydrogen peroxide to water and oxygen. Oxygen forms on the filter paper, and the filter paper rises to the top of the beaker. Catalase activity is measured by timing the rise of the enzyme-soaked filter paper to the top of beakers containing different concentrations of hydrogen peroxide. Johnson, A. Kristin. J. Chem. Educ.2000, 77, 1451.

Enzymes |

Kinetics |

Proteins / Peptides |

Reactions

Combustion Demonstration Using Updated Flame TornadoEdward G. SenkbeilThis demonstration uses the combustion of different forms of cellulose and an updated version of the "flame tornado" as an ignition source to illustrate the factors affecting the combustion process. The objectives of the experiment are to illustrate the factors affecting the rate of a combustion reaction and to demonstrate the factors affecting the production of a flame by using the flame tornado. Senkbeil, Edward G. J. Chem. Educ.2000, 77, 1449.

Descriptive Chemistry |

Oxidation / Reduction |

Reactions |

Rate Law

Periplanar or Coplanar?Saul Kane and William H. HershThe prefix peri, derived from the Greek for "near", was chosen to make the meaning "approximately planar". However, the current common usage of syn and antiperiplanar is planar, which is incorrect. In the interests of proper language, we suggest that future authors instead use "syn-coplanar" and "anti-coplanar".Kane, Saul; Hersh, William H. J. Chem. Educ.2000, 77, 1366.

When A + B B + AErling Antony, Lindsay Mitchell, and Lauren NettenstromMany acid-base chemistry demonstrations and laboratory manuals include the "baking soda volcano". Others use the formation of calcium carbonate from calcium hydroxide and carbon dioxide in human breath. This demonstration uses principles from both as well as stoichiometry to answer the question "Does the order of mixing of reagents make a difference?" Antony, Erling; Mitchell, Lindsay; Nettenstrom, Lauren. J. Chem. Educ.2000, 77, 1180.

Acids / Bases |

Stoichiometry |

Reactions

Kinetic Isotope Effect in the Chromic Acid Oxidation of Secondary AlcoholsCharles E. Harding, Christopher W. Mitchell, and Jozsef DevenyiThe kinetic isotope effect is an invaluable tool in studying certain organic reaction mechanisms. Two activities involving the technique that are suitable for introductory organic laboratory students are described. A simple competition experiment utilizing the benzhydrol?benzhydrol-d1 system and chromic acid oxidation is used to demonstrate qualitatively that there is a kinetic isotope effect involved in this process. Harding, Charles E.; Mitchell, Christopher W.; Devenyi, Jozsef. J. Chem. Educ.2000, 77, 1042.

Photochemistry of Chloropicrin. A Physical Chemistry ProjectE. A. Wade, T. P. Clemes, and K. A. SingmasterIn this experiment, students will use FTIR spectroscopy to monitor the kinetics of the photolysis of chloropicrin by an Hg arc lamp, both with and without oxygen. They will then be able to determine the mechanism of the photolytic reaction. Wade, Elisabeth A.; Clemes, T. P.; Singmaster, Karen A. J. Chem. Educ.2000, 77, 898.

Atmospheric Chemistry |

IR Spectroscopy |

Kinetics |

Photochemistry |

Mechanisms of Reactions

Elucidation of Molecular Structure Using NMR Long-Range Coupling: Determination of the Single Isomer Formed in a Regiospecific ReactionSamuel Delagrange and Françoise NepveuThe experiment presented in this article introduces students to the main concepts of two essential NMR techniques for investigating molecular structure. Heteronuclear multiple bond connectivity (HMBC) and proton-coupled 13C NMR are used to determine which isomer, from a possible two, is formed by a regiospecific reaction. The demonstration, based on long-range coupling between quaternary carbons and protons on neighboring carbons, is presented step by step. Delagrange, Samuel; Nepveu, Françoise. J. Chem. Educ.2000, 77, 895.

Molecular Properties / Structure |

NMR Spectroscopy |

Synthesis |

Carboxylic Acids |

Reactions |

Diastereomers

The Story of the Wagner-Meerwein RearrangementLudmila BirladeanuThis paper tells the story of the long, arduous journey toward comprehending the mechanism of molecular rearrangements. This work involved the greatest chemists of the 19th and 20th centuries, among whom two names stand out: Georg Wagner, who showed what happens in these strange reshufflings of atoms, and Hans Meerwein, who showed how it happens. The resulting insight revolutionized the theory of organic chemistry. Birladeanu, Ludmila. J. Chem. Educ.2000, 77, 858.

Reaction of Dibenzoylethylene with Hydriodic AcidFred H. GreenbergDibenzoylethylene is treated with hydriodic acid in acetone at room temperature to obtain dibenzoylethane rather than the expected dibenzoyliodoethane. Students identify the product by the use of NMR and IR spectra and are given a nonpictorial representation of a mechanism and asked to supply the structures of the relevant intermediates. Greenberg, Fred H. J. Chem. Educ.2000, 77, 505.

Organic Reaction Animations, Version 1.5, CD-ROM (by Steven A. Fleming, Paul B. Savage, and Greg R. Hart)reviewed by Michael S. HoldenAccompaniment to Organic Chemistry by the same authors. Fifty animations that can be viewed in a ball-and-stick, space-filling, HOMO, or LUMO mode. The animations can be put on a slow-motion setting to permit better visualization and are accompanied by an energy diagram, making it easy to identify transition states and intermediates. Electron flow is apparent in the HOMO and LUMO modes, allowing the student to link curved arrows and orbital interactions. Holden, Michael S. J. Chem. Educ.2000, 77, 447.

Reactions |

Mechanisms of Reactions |

Reactive Intermediates

Molecular Modeling to Predict Regioselectivity of Hydration ReactionsKate J. Graham, Kathleen Skoglund, Chris P. Schaller, William P. Muldoon, and John B. KlassenStudents oxidize several isomeric alkenes using acid-catalyzed hydration, oxymercuration/demercuration, and hydroboration to compare the regioselectivity of the different techniques. The product mixtures are subsequently analyzed by GC and IR. To explain the results fully, students use the Spartan 5.0 molecular modeling package to predict the regioselectivity of these hydration reactions. Graham, Kate J.; Skoglund, Kathleen; Schaller, Chris P.; Muldoon, William P.; Klassen, John B. J. Chem. Educ.2000, 77, 396.

Computational Chemistry |

Mechanisms of Reactions |

Reactive Intermediates |

IR Spectroscopy |

Gas Chromatography |

Molecular Recognition |

Molecular Properties / Structure |

Molecular Modeling

Multicomponent Reactions: A Convenient Undergraduate Organic Chemistry ExperimentRicardo Bossio, Stefano Marcaccini, Carlos F. Marcos, and Roberto PepinoTwo experiments for the synthesis of a -lactam and a succinimide, based on a 4-component Ugi condensation. The experimental procedures for both syntheses are identical except for the choice of the starting amine, whose electron richness is controlled by the presence or absence of an electron-withdrawing group. Bossio, Ricardo; Marcaccini, Stefano; Marcos, Carlos F.; Pepino, Roberto. J. Chem. Educ.2000, 77, 382.

Synthesis |

Drugs / Pharmaceuticals |

IR Spectroscopy |

NMR Spectroscopy |

Mechanisms of Reactions |

Molecular Properties / Structure

Introducing Chiroscience into the Organic Laboratory CurriculumKenny B. Lipkowitz, Tim Naylor, and Keith S. Anliker"Chiroscience" is a young but robust industry linking science and technology with chemistry and biology; includes description of an asymmetric reduction of a ketone followed by an assessment of the enantiomeric excess by GC using a chiral stationary phase.Lipkowitz, Kenny B.; Naylor, Tim; Anliker, Keith S. J. Chem. Educ.2000, 77, 305.

Chirality / Optical Activity |

Chromatography |

Mechanisms of Reactions |

Synthesis |

Separation Science |

Stereochemistry |

Gas Chromatography |

Aldehydes / Ketones

Computational Investigations for Undergraduate Organic Chemistry: Predicting the Mechanism of the Ritter ReactionRita K. HessleyBefore carrying out a laboratory experiment that investigates the mechanism for the formation of N-t-butylbenzamide, students construct and obtain heats of formation for reactants, products, postulated reaction intermediates, and one transition state structure for each proposed mechanism. This is designed as a companion to an open-ended laboratory experiment that hones skills learned early in most traditional organic chemistry courses.Hessley, Rita K. J. Chem. Educ.2000, 77, 202.

Keep Going with Cyclooctatetraene!Addison AultThis paper shows how some simple properties of cyclooctatetraene can indicate important ideas about the structure of cyclooctatetraene.Ault, Addison. J. Chem. Educ.2000, 77, 55.

Organizing Organic Reactions: The Importance of Antibonding OrbitalsDavid E. LewisIt is proposed that unoccupied molecular orbitals arbitrate much organic reactivity, and that they provide the basis for a reactivity-based system for organizing organic reactions. Such a system is proposed for organizing organic reactions according to principles of reactivity, and the system is discussed with examples of the frontier orbitals involved. Lewis, David E. J. Chem. Educ.1999, 76, 1718.

Covalent Bonding |

Mechanisms of Reactions |

MO Theory

Techniques and Experiments for Organic Chemistry, 6th Edition (by Addison Ault)reviewed by Karen C. InmanThose who may be new to Ault's text will find a well-written laboratory manual that clearly reflects the author's years of experience. It is thorough, describing all the common lab techniques in Part 1 and giving concise, well-written directions for experiments in Part 2. The experiments provide an excellent representation of all the important reactions in a typical course. In fact, for most types of reactions there are several experiments from which to choose. Inman, Karen C. J. Chem. Educ.1999, 76, 1629.

Preparation and Identification of Benzoic Acids and Benzamides: An Organic "Unknown" LabDouglass F. Taber, Jade D. Nelson, and John P. NorthropThe reaction of an unknown substituted benzene derivative with oxalyl chloride and aluminum chloride gives the acid chloride. Hydrolysis of the acid chloride gives the acid, and reaction of the acid with concentrated aqueous ammonia gives the benzamide. The equivalent weight of the acid can be determined by titration; given this information and the melting points of the acid and the benzamide, it is possible to deduce the structure of the initial unknown. Taber, Douglass F.; Nelson, Jade D.; Northrop, John P. J. Chem. Educ.1999, 76, 828.

Organic Chemistry (by Joseph M. Hornback)R. Daniel LibbyThis text uses reaction mechanisms as the organizing principle, introduces structure where it is necessary to support the reactions to be studied, and considers synthesis after the mechanisms of appropriate reactions have been discussed. Libby, R. Daniel. J. Chem. Educ.1999, 76, 611.

A Safe Simple Halogenation ExperimentHilton M. Weiss and Lara GanzThis experiment is designed to be a safe and experimentally simple procedure appropriate to the early weeks of a course when halogenation is the only reaction which has been discussed in the lecture. It can also provide some early experience with simple interpretation of NMR spectra. Weiss, Hilton M.; Ganz, Lara. J. Chem. Educ.1999, 76, 534.

Synthesis |

Free Radicals |

Reactions |

NMR Spectroscopy

Using Large Glass Cylinders To Demonstrate Chemical ReactionsWobbe de VosThis article describes a simple laboratory experiment that aims at pedagogic as well as aesthetic aspects of chemical reactions. Experiments of this type have a high educational potential as students have the opportunity to observe the actual formation of a precipitate instead of just being able to see the result. The experiment is also suitable for demonstrating some of the fascinating beauty of chemical reactions to the general public.de Vos, Wobbe. J. Chem. Educ.1999, 76, 528.

General Potential Energy Surfaces for Catalytic ProcessesS. H. BauerHere we argue that one may describe, in general terms, how catalysts modify reaction mechanisms by entering and leaving a conversion sequence, using potential energy surfaces that are conceptually correct. Thermochemical and kinetic constraints providing bounds that limit catalytic processes are formulated. 3-D diagrams are proposed. These clearly illustrate the basic principle that catalysts initially associate with the substrates and thus directly participate in modified conversion pathways, but are regenerated in the final step, thereby providing for a turnover number greater than unity. Bauer, S. H. J. Chem. Educ.1999, 76, 440.

Catalysis |

Kinetics |

Mechanisms of Reactions

The Ammonia Smoke Fountain: An Interesting Thermodynamic AdventureM. Dale AlexanderThe ammonia smoke fountain demonstration utilizes a modification of the apparatus used in the standard ammonia fountain. The modification allows for the introduction of hydrogen chloride gas into a flask of ammonia rather than water. The flow rate of hydrogen chloride gas into the flask in the smoke fountain is not constant, but periodic; that is, the smoke puffs from the end of the tube. This unexpected behavior elicits an interesting thermodynamic explanation.Alexander, M. Dale. J. Chem. Educ.1999, 76, 210.

Acids / Bases |

Gases |

Thermodynamics |

Reactions |

Stoichiometry |

Precipitation / Solubility

Understanding Organic Reaction Mechanisms (by Adam Jacobs)Daniel BergerA good buy for any organic chemist, particularly for those teaching organic chemistry, and should be strongly considered as a supplementary text. It is also useful as a main text (supplemented by other material) for an intermediate-to-advanced undergraduate course in organic reaction mechanisms.Berger, Daniel. J. Chem. Educ.1999, 76, 167.

Side Reactions in a Grignard SynthesisHilton M. WeissThis experiment describes a standard Grignard synthesis of a secondary alcohol, 3-heptanol. It brings attention to a significant side product, 3-heptanone, and suggests ways of understanding and utilizing the formation of this product. The experiment is intended to stimulate creative thought in the undergraduate organic chemistry course. Weiss, Hilton M. J. Chem. Educ.1999, 76, 76.

Mechanisms of Reactions |

Synthesis |

Grignard Reagents

The Design and Synthesis of a Large Interactive ClassroomLaurel L. Clouston and Mark H. KleinmanThe use of group learning techniques in large classes has been used to effectively convey the central concepts of SN1 and SN2 reactions in an introductory organic chemistry class. The activities described are best used as an introduction to these mechanisms. Clouston, Laurel L.; Kleinman, Mark H. J. Chem. Educ.1999, 76, 60.

Mechanisms of Reactions |

Learning Theories

The Pechmann ReactionMichael S. Holden and R. David CrouchA solid acid-catalyzed version of the Pechmann reaction for the synthesis of coumarins is described. The Pechmann reaction is a multiple-transformation process which is not a part of the normal organic chemistry curriculum.Holden, Michael S.; Crouch, R. David. J. Chem. Educ.1998, 75, 1631.

Catalysis |

Mechanisms of Reactions |

Microscale Lab |

Synthesis |

Reactions |

Phenols

Inadequacies of the SN1 MechanismJohannes DaleA planar free carbocation intermediate is used as a simple model to explain racemization in solvolysis; but the problem is that racemization is never complete, the enantiomer in excess having the inverted configuration. Also, the unimolecularity has never been demonstrated, but is an assumption only. Dale, Johannes. J. Chem. Educ.1998, 75, 1482.

Mechanisms of Reactions

Organic Reactions Involving Bromine: Puzzles for the Organic LaboratorySarita I. McGowens and Ernest F. SilversmithFive puzzles for the organic chemistry laboratory are described. All involve bromine, which is generated in a safe, convenient way that makes it possible to control the amount of bromine precisely. Three of the puzzles involve orientation in electrophilic aromatic substitution, one is a determination of the stereochemistry of addition to alkenes, and the other one looks at the possibility of dehydrohalogenation following addition. McGowens, Sarita I.; Silversmith, Ernest F. J. Chem. Educ.1998, 75, 1293.

NMR Spectroscopy |

Synthesis |

Stereochemistry |

Mechanisms of Reactions

A Modified Synthesis of the Insect Repellent DEETPeter H. Knoess and Edward G. NeelandIn the preparation of the insect repellent DEET, lab procedures prepare the intermediate m-toluoyl chloride by heating m-toluic acid with thionyl chloride for times ranging from 15 to 45 minutes. The acid chloride is then worked up under Schotten-Baumann conditions to yield DEET.Knoess, Peter H.; Neeland, Edward G. J. Chem. Educ.1998, 75, 1267.

Slide Projector Corrosion CellSilvia Tejada, Estela Guevara, and Esperanza OlivaresThe process of corrosion can be demonstrated in a slide projector, since the cell is in the shape of a slide, or on the stage of an overhead projector by setting up a simple galvanic cell. Corrosion occurs as the result of a galvanic cell reaction, in which the corroding metal acts as the anode. Several simple demonstrations relating to corrosion are described here.Tejada, Silvia; Guevara, Estela; Olivares, Esperanza. J. Chem. Educ.1998, 75, 747.

Kinetic Demonstration of Intermolecular General Acid (GA) Catalysis in Thiolysis of 9-Anilinoacridine Mohammad Niyaz KhanAfter nearly five decades of active research and numerous publications on GA-GB catalysis, introduction of an experiment on GA for students majoring in enzymology/physical organic chemistry at advanced undergraduate/postgraduate level is appropriate. A kinetic experiment involving the reaction of 2-mercaptoethanol (2-ME) with 9-anilinoacridine (9-ANA) is designed to demonstrate intermolecular GA catalysis. Khan, Mohammad Niyaz. J. Chem. Educ.1998, 75, 632.

Bioinorganic Chemistry |

Bioorganic Chemistry |

Mechanisms of Reactions |

Catalysis |

Acids / Bases |

Kinetics

A History of the Double-Bond RuleBernard E. HoogenboomFrom his experience as an industrial chemist, Otto Schmidt recognized the bond weakening in hydrocarbons and in 1932 postulated the "Double-Bond Rule," stating that the presence of a double bond in a hydrocarbon has an alternating strengthening and weakening effect on single bonds throughout the molecule, diminishing with distance from the double bond.Hoogenboom, Bernard E. J. Chem. Educ.1998, 75, 596.

Learning Theories |

Mechanisms of Reactions |

Alkenes

Mechanism Templates: Lecture Aids for Effective Presentation of Mechanism in Introductory Organic ChemistryBrian J. McNelisTo promote active student learning of mechanism in introductory organic chemistry, hand-outs have been developed with incomplete structures for reaction processes depicted, which are called mechanism templates. The key to these lecture aids is to provide only enough detail in the diagram to facilitate notetaking, ensuring that these templates are dynamic learning tools that must be utilized by an engaged and alert student.Brian J. McNelis. J. Chem. Educ.1998, 75, 479.

Learning Theories |

Mechanisms of Reactions |

Reactions |

Addition Reactions |

Acids / Bases |

Electrophilic Substitution |

Nucleophilic Substitution

Incorporating Organic Name Reactions and Minimizing Qualitative Analysis in an Unknown Identification ExperimentClaire Castro and William KarneyThe authors have developed a new type of unknown identification experiment for the introductory organic chemistry laboratory. The unknown sample the student is provided with is the product of an organic name reaction. The student is only informed of the starting material and conditions used in the compound's synthesis, and must then: (1) deduce the compound's structure, (2) determine the name reaction and corresponding mechanism that yields the compound, and (3) present his/her results to the class. Claire Castro and William Karney. J. Chem. Educ.1998, 75, 472.

What are Isodesmic Reactions?D. A. Ponomarev and V. V. TakhistovThe heat of isodesmic (formal) reaction Q is systematically used as a measure of deviations from the additivity of bond energies. For molecules these Q values are applied to quantification of strain energies in cyclic compounds, to evaluation of aromaticity of benzene, to explanation of the reasons for deviation from additivity in the heats of formation for disubstituted benzenes and some alkenes.Ponomarev, D. A.; Takhistov, V. V. J. Chem. Educ.1997, 74, 201.

Reactions |

Molecular Properties / Structure

A -78°C Sequential Michael Addition for the Organic LabMichael W. TanisThis paper introduces a cold-temperature enolate alkylation reaction that can be performed safely and inexpensively by undergraduate students in approximately two 3-hour lab sessions. Tanis, Michael W. J. Chem. Educ.1997, 74, 112.

Addition Reactions |

Alkenes |

Aldehydes / Ketones |

Synthesis

Reduction of Carboxylic Acids with Sodium Borohydride and an ElectrophileJan William Simek, Thad Tuck, and Kelly Courter BushIntegration of new reduction conditions into a procedure applicable to the first-year organic chemistry laboratory, where reduction of the carboxylic acid group has remained an obstacle, notwithstanding the use of borane or LiAlH4 (2) on the microscale. The NaBH4 method with either electrophile can be modified to any scale; in our hands, the use of I2 as the electrophile performed better at the semimicro scale than the H2SO4 method. Simek, Jan William; Tuck, Thad; Bush, Kelly Courter . J. Chem. Educ.1997, 74, 107.

Carboxylic Acids |

Aromatic Compounds |

Oxidation / Reduction

Organic Chemistry, Third Editionreviewed by Timothy D. LashThe author continues to stress the use of reaction mechanisms, and this remains a strong point in the new edition. The heart and soul of modern organic chemistry revolves around these concepts, and this framework is essential for a textbook of this type. Lash, Timothy D. J. Chem. Educ.1996, 73, A312.

Carbonyl and Conjugate Additions to Cyclohexenone: Experiments Illustrating Reagent SelectivityMichael G. Organ and Paul AndersonUndergraduate students leaving an organic chemistry program should have exposure to these concepts and hands-on experience in dealing practically with the issue of selectivity. In this paper, selective addition of a nucleophile to either end of the enone moiety in cyclohexenone is examined. Organ, Michael G.; Anderson, Paul. J. Chem. Educ.1996, 73, 1193.

Addition Reactions |

Aldehydes / Ketones |

Mechanisms of Reactions

An Organoleptic Laboratory ExperimentJohn M. RisleyCompounds in ten different classes of organic molecules that are used in the fragrance and food industry are provided to students. Students whiff the vapors of each compound and describe the organoleptic properties using a set of terms utilized in the fragrance and food industry. A set of questions guides students to an understanding of the relationship between structure of molecules and smell.Risley, John M. J. Chem. Educ.1996, 73, 1181.

Propylene Oxide Addition to Hydrochloric Acid: A Textbook ErrorRebecca E. Phillips and Robert L. Soulen Procedure illustrating organic synthesis involving propylene oxide, a major industrial chemical, and important features of the SN1 and SN2 mechanisms (there are some differences on how this reaction is described in several organic textbooks). Phillips, Rebecca E.; Soulen, Robert L. J. Chem. Educ.1995, 72, 624.

Is This Reaction a Substitution, Oxidation-Reduction, or Transfer?Imyanitov, Naum S.Author argues that separation of chemical reaction types based on convention do not always follow objective and consistent rules. This leads to confusion among students and artificial borders within the various sub-disciplines in chemistry.Imyanitov, Naum S. J. Chem. Educ.1993, 70, 14.

Reaction dynamicsLacks, DanielSoftware that simulates collisions of an atom with a diatomic molecule, allowing students to set the initial conditions and the type of atom or molecule involved.Lacks, Daniel J. Chem. Educ.1992, 69, 1010.

Enzyme activity: The ping-pong ball torture analogyHelser, Terry L.The author uses this analogy to help students visualize and understand the effect of reaction conditions on the initial rate of an enzyme-catalyzed reaction.Helser, Terry L. J. Chem. Educ.1992, 69, 137.

Enzymes |

Reactions

The conversion of chemical energy: Part 1. Technological examplesWink, Donald J.When a chemical reaction occurs, the energy of the chemical species may change and energy can be released or absorbed from the surroundings. This can involve the exchange of chemical energy with another kind of energy or with another chemical system.Wink, Donald J. J. Chem. Educ.1992, 69, 108.

Reaction of bromine with hydrocarbons on the overhead, real or simulatedSolomon, Sally; Gregory, Michael; Padmanabhan, Sandeep; Smith, KurtA simulation that looks like the addition of bromine to hydrocarbons but is not (the bromine is simulated using a mixture of food colorings).Solomon, Sally; Gregory, Michael; Padmanabhan, Sandeep; Smith, Kurt J. Chem. Educ.1990, 67, 961.

A catalog of reactions for general chemistryTykodi, R. J.A catalog of chemical reactions intended to help students understand what kinds of chemical reactions commonly occur and why.Tykodi, R. J. J. Chem. Educ.1990, 67, 665.

Three easy puzzles based on the Diels-Alder reactionPickering, Miles.This paper recasts some classic systems so that they can be done at room temperature on a small scale in a large lab course without sophisticated instrumentation. Furthermore, they start the student using experimental results to solve mechanistic problems.Pickering, Miles. J. Chem. Educ.1990, 67, 524.

A small scale equilibrium experiment Flash, PatrickAn alternative method for the experiment in which the equilibrium constant for the iron-thiocyanate complex is determined.Flash, Patrick J. Chem. Educ.1990, 67, 341.

Organic Reaction Chemistry, Review II (Flash, P.; Bendall, V.)Chipman, Wilmon B.Six different programs which allow the user to identify functional groups, supply the missing reagent necessary to complete a given reaction, deduce the product of a given reaction, ascertain whether a given reaction will go, search the reaction database for functional group conversions, and search for the utility of a certain reagent.Chipman, Wilmon B. J. Chem. Educ.1989, 66, A171.

Enrichment / Review Materials |

Reactions |

Mechanisms of Reactions |

Nomenclature / Units / Symbols

Organic Reaction Chemistry, Review I (Flash, P.; Bendall, V.)Hargis, J. H.Six different programs which allow the user to identify functional groups, supply the missing reagent necessary to complete a given reaction, deduce the product of a given reaction, ascertain whether a given reaction will go, search the reaction database for functional group conversions, and search for the utility of a certain reagent.Hargis, J. H. J. Chem. Educ.1989, 66, A170.

A study of the E2 reaction for the microscale organic labFlash, Patrick; Galle, Fred; Radil, MarkStudents determine the pseudo-first-order rate constant for the elimination of HBr from 2-bromobutane and measure the yield and approximate composition of the alkene products, determine the yield of alkenes from 1-bromobutane under the same conditions, and examine the effect of changing solvent polarity on alkene yields for the two halides.Flash, Patrick; Galle, Fred; Radil, Mark J. Chem. Educ.1989, 66, 958.

Cobalt(II) and cobalt(III) coordination compoundsThomas, Nicholas C.; Pringle, Katrina; Deacon, Glen B.This experiment illustrates the formation of tris(phenanthroline)cobalt complexes in the +2 and +3 oxidation states, the effect of coordination on reactions of the ligand, and the use of a ligand displacement reaction in recovering the transformed ligand.Thomas, Nicholas C.; Pringle, Katrina; Deacon, Glen B. J. Chem. Educ.1989, 66, 516.

Coordination Compounds |

Crystal Field / Ligand Field Theory |

Mechanisms of Reactions

The interconversion of cis and trans isomersMcGinn, Clifford J.; Wheatley, William B.Trans-alkene oxides are converted to cis-alkenes on treatment with tributylphosphine, yet this reaction does not appear in most organic textbooks.McGinn, Clifford J.; Wheatley, William B. J. Chem. Educ.1989, 66, 486.

Stereochemistry |

Diastereomers |

Alkenes |

Mechanisms of Reactions

On a Reaction Involving Oxygen and Metal SulfidesHill, William D., Jr.The role of iron(III) oxide as a catalyst in the production of oxygen by the thermal decomposition of potassium chlorate promoted the idea to use this oxide to repeat the reactions involving oxygen and the metal sulfides described in an earlier article.Hill, William D., Jr. J. Chem. Educ.1989, 66, 448.

A classroom demonstration of aliphatic substitution Perina, Ivo; Mihanovic, BrankaSubstitution of an alkane by a halogen can be demonstrated effectively on the stage of an overhead projector using a compartmentalized Petri dish or a transparent Conway dish covered by a glass platePerina, Ivo; Mihanovic, Branka J. Chem. Educ.1989, 66, 257.

Oscillating chemical reactions and nonlinear dynamicsField, Richard J.; Schneider, F. W.The field of oscillating chemical reactions has grown dramatically over the last 15 years. The reasons for this activity are the intrinsic chemical interest in the behavior and mechanisms of oscillating chemical reactions and the connection between oscillating reactions and the properties of nonlinear differential equations.Field, Richard J.; Schneider, F. W. J. Chem. Educ.1989, 66, 195.

Reactions |

Equilibrium |

Mechanisms of Reactions

The language of dynamicsField, Richard J.For a reacting chemical system, there exists a set of polynomial differential equations that describes the dynamics of how the concentrations of all chemical species change with time.Field, Richard J. J. Chem. Educ.1989, 66, 188.

In pursuit of chemical literacy: A place for chemical reactionsBond, DouglasThe author has described one method of implementing a course for nonscience majors in which an early and repeated exposure to chemical reactions in tandem with a set of scientific values is the key to approaching scientific literacy.Bond, Douglas J. Chem. Educ.1989, 66, 157.

Decarboxylation of a keto acidsHanson, R. W.Rectifies the lack of information concerning the nonenzymatic decarboxylation of alpha-keto acids found in many textbooks and to correct errors found in others.Hanson, R. W. J. Chem. Educ.1987, 64, 591.

The arsenic(III) sulfide clock reactionWatkins, Kenneth W.Two colorless solutions, one containing sodium arsenite and acetic acid and the other containing sodium thiosulfate are mixed in a beaker; after about 20 seconds, the mixture turns a brilliant yellow color. This clock reaction is well suited for determining the order of reaction and the activation energy.Watkins, Kenneth W. J. Chem. Educ.1987, 64, 255.

Selective oxidation in the presence of a heterocycleBowles, K. Dean; Quincy, David A.; McKenna, John I.; Natale, N. R.The process of weighing the advantages and disadvantages of various oxidation methods are presented in this paper.Bowles, K. Dean; Quincy, David A.; McKenna, John I.; Natale, N. R. J. Chem. Educ.1986, 63, 358.

Alcohols |

Aldehydes / Ketones |

Heterocycles |

Oxidation / Reduction |

Carboxylic Acids

A multipurpose, dramatic combustion effectFenster, Ariel E.; Harpp, David N.; Dore, Marcel; Schwarcz, Joseph A.A powerful demonstration on combustion that has been used in and out of the classroom is described in this note.Fenster, Ariel E.; Harpp, David N.; Dore, Marcel; Schwarcz, Joseph A. J. Chem. Educ.1986, 63, 349.

Interstellar chemistryCarbo, R.; Ginebreda, A.Surveys some of the features that characterize interstellar chemistry, particularly the composition of the interstellar medium and the nature of the changes that occur there.Carbo, R.; Ginebreda, A. J. Chem. Educ.1985, 62, 832.

Astrochemistry |

Gases |

Reactions |

Mechanisms of Reactions

Uncertainty in establishing a reaction intermediateMartin, R. BruceShows the difficulty of proving that a compound whose concentration passes through a maximum is necessarily an intermediate on the pathway from initial reactants to products.Martin, R. Bruce J. Chem. Educ.1985, 62, 789.

"Name that product"-A lively organic chemistry reviewMattern, Daniell LewisA review activity in which students reveal a hidden reaction on the overhead by answering individual questions regarding various topics; once the hidden reaction is revealed, they must determine its product.Mattern, Daniell Lewis J. Chem. Educ.1985, 62, 476.

A short set of 13C-NMR correlation tablesBrown, D. W.The object of these tables is to enable a student to calculate rapidly approximate d values for 13C nuclei in as wide a variety of compounds as possible.Brown, D. W. J. Chem. Educ.1985, 62, 209.

Structure elucidation of a natural productLetcher, Roy M.This experiment is an attempt to simulate a real-life structure elucidation problem through the isolation, characterization, and chemical transformation of an unknown naturally occurring monoterpene, with extensive use being made of spectroscopy and aided by biogenetic considerations.Letcher, Roy M. J. Chem. Educ.1983, 60, 79.

Bent thermometerSmith, Douglas D.Reducing the breakage of thermometers, using CO2 as an insecticide, and improving the demonstration of the reaction between sodium and water.Smith, Douglas D. J. Chem. Educ.1979, 56, 742.

A dynamic carbon model capable of showing changes in hybridizationFountain, K. R.It is possible to construct a simple dynamic model of a carbon atom that demonstrates the Walden inversion, the SN1 reaction, and when joined with another units like itself demonstrates the full spectrum of elimination reactions.Fountain, K. R. J. Chem. Educ.1979, 56, 379.

Favorskii rearrangement in bridged polycyclic compoundsChenier, Philip J.Favorskii rearrangement in bridged polycyclic compounds: This can be classified as an intramolecular rearrangement from carbon to carbon, involving a migrating group Z moving without its electrons from migrating origin A to an electron-rich terminus B.Chenier, Philip J. J. Chem. Educ.1978, 55, 286.

Organic photochemistryZimmerman, H. E.In this question, students must recognize that the protonated zwitterion is more likely to react with an external nucleophile than with the internal center of negative charge on the zwitterion.Zimmerman, H. E. J. Chem. Educ.1977, 54, 756.

Photochemistry |

Mechanisms of Reactions

Selectivity and specificity in organic reactionsAult, AddisonDistinguishes between various forms of selectivity and specificity (e.g. the us of and differences between stereoselective and stereospecific).Ault, Addison J. Chem. Educ.1977, 54, 614.

Vitalizing the lecture. Lap-dissolve projectionHarpp, David N.; Snyder, James P.Describes and provides examples of the lap-dissolve effect, a technique that uses two 35mm slide projectors to convey changing images in a large lecture setting.Harpp, David N.; Snyder, James P. J. Chem. Educ.1977, 54, 68.

Molecular Properties / Structure |

Mechanisms of Reactions

Teaching aromaticity, conjugation, and enolizationSchambach, Robert A.An understanding of the delocalization of electrons in organic compounds is central knowledge. In teaching undergraduates about aromaticity, conjugation, and enoliztion, this author has found it useful to present examples of compounds in which delocalization. Effects are sustained in the presence of potentially interfering saturated carbon atoms.Schambach, Robert A. J. Chem. Educ.1976, 53, 711.

Grignard dehydration reactions. An undergraduate organic experiment.Duty, Robert C.; Ryder, Bernard L.In this laboratory, the authors have incorporated the Grignard reaction in a step-wise synthesis that has been successful in demonstrating several experimental and instrumental techniques.Duty, Robert C.; Ryder, Bernard L. J. Chem. Educ.1976, 53, 457.

Two examples of programmed learning in inorganic chemistryKaufmann-Goetz, H.; Kaufmann, G.This paper looks to described a program allowing students in inorganic chemistry to learn individually and requiring them to reflect and participate. They go on to demonstration a simulation of the kinetic study of a chemical reaction.Kaufmann-Goetz, H.; Kaufmann, G. J. Chem. Educ.1976, 53, 179.

Photolysis of a heterocyclic compound. An advanced undergraduate experimentJarrar, Adil A.This experiment is adapted to suit an organic chemistry introduction course and may be introduced near the final stages when the students have acquired the ability to speculate about the mechanisms of the reactions involved. Students appreciated working with small quantities of beautifully crystalline solids.Jarrar, Adil A. J. Chem. Educ.1974, 51, 755.

Reactions |

Crystals / Crystallography |

Heterocycles

A novel photochemistry experiment using a Diels-Alder reactionNash, E. G.The authors present a two-step experiment incorporating a novel, but general photochemical reaction that is rapid, does not require special equipment, and which yields an interesting product worthy of further study.Nash, E. G. J. Chem. Educ.1974, 51, 619.

Polymerization as a model chain reactionMorton, MauriceThe building of long chain macromolecules offers the best opportunity for the study of chain reactions and the free radical mechanism.Morton, Maurice J. Chem. Educ.1973, 50, 740.

A new method for learning organic reactionsPerlmutter, Howard D.; Kristol, David S.Using wooden cubes in a game to help students learn organic reactions.Perlmutter, Howard D.; Kristol, David S. J. Chem. Educ.1972, 49, 793.

Reactions |

Mechanisms of Reactions |

Synthesis

Pseudo first-order kineticsCorbett, John F.A kinetic study of second-order reactions under first-order conditions can yield accurate second-order rate constants provided an empirical allowance is made for the depletion of the reactant in excess.Corbett, John F. J. Chem. Educ.1972, 49, 663.

Migratory aptitudes. An organic chemistry experimentZaczek, Norbert M.; Ruff, James C.; Jackewitz, Albert H.; Roswell, David F.The authors share a set of reactions and analysis that illustrates to students not only a rearrangement reaction by also reinforces the concept of migratory aptitude discussed in the classroom.Zaczek, Norbert M.; Ruff, James C.; Jackewitz, Albert H.; Roswell, David F. J. Chem. Educ.1971, 48, 257.

Nonlinear Hammett relationshipsSchreck, James 0.The author provides examples of nonlinear structure-reactivity , Hammett correlation's, and summarize most of the types of reactions in which deviations due to change in mechanism or rate-controlling step occur.Schreck, James 0. J. Chem. Educ.1971, 48, 103.

Catalysis demonstrations with Cr2O3Briggs, Thomas S.Cr2O3 is used as a catalyst in the oxidation of nonflammable substances such as glycerine and glacial acetic acid.Briggs, Thomas S. J. Chem. Educ.1970, 47, A206.

Fluorine compounds as teaching aids in organic theoryYoung, John A.Fluorine compounds do obey the fundamental tenets of organic theory, but their frequent reversal of polarity, relative to hydrocarbon analogs, and the change in emphasis from a positive hydrogen ion to a negative fluoride ion allow the instructor to frame questions that demand reasoning rather than reiteration on the part of the student.Young, John A. J. Chem. Educ.1970, 47, 733.

Aromatic Compounds |

Mechanisms of Reactions

Donor-acceptor interactions in organic chemistrySunderwirth, S. G.The purpose of this article is to aid teachers in making even more effective use of theoretical considerations in teaching organic chemistry; the primary objective is to emphasize the underlying principles that are common to the following four basic types of reactions: substitution, addition, elimination, and rearrangement.Sunderwirth, S. G. J. Chem. Educ.1970, 47, 728.

The hexaphenylethane landmark fallsSmith, William B.A reexamination of Gomberg's discovery that the treatment of triphenylmethyl chloride with silver results in hexaphenylethane has demonstrated that the dimer formed is not hexaphenylethane; a new product has been proposed.Smith, William B. J. Chem. Educ.1970, 47, 535.

Energy of activationIdoux, John P.Spinning a half sphere until it comes to a rest on its flat side serves as an analogy to a system of molecules that must acquire a certain amount of energy until they become products.Idoux, John P. J. Chem. Educ.1969, 46, A547.

Identification of an unknown ester: An analytical-organic experimentGrob, Robert L.; Husk, G. RonaldIt is the student's challenge to hydrolyze an ester, separate and purify the resultant alcohol and acid, determine several physical and chemical characteristics, and arrive at a logical choice for its identity.Grob, Robert L.; Husk, G. Ronald J. Chem. Educ.1969, 46, 769.

Encounters and slow reactionsLangford, Copper H.This paper reviews the formation of a metal ion and a ligand in a mechanistic language, as much derived from the collision theory as from transition state theory.Langford, Copper H. J. Chem. Educ.1969, 46, 557.

Bimolecular nucleophilic displacement reactionsEdwards, John O.The bimolecular nucleophilic displacement reaction is important and should be included in any detailed discussion of kinetics and mechanism at an early undergraduate level.Edwards, John O. J. Chem. Educ.1968, 45, 386.

Reactions |

Nucleophilic Substitution |

Kinetics |

Mechanisms of Reactions

From stoichiometry and rate law to mechanismEdwards, John O.; Greene, Edward F.; Ross, JohnExamines the rules used by chemists as guidelines in developing mechanisms from stoichiometric and rate law observations. Edwards, John O.; Greene, Edward F.; Ross, John J. Chem. Educ.1968, 45, 381.

The stoichiometry of an oxidation-reduction reactionLatimer, George W., Jr.A short note on the titration of hydrazine sulfate with standard bromate in the presence of sodium molybdate that requires students to identify the products through the use of some elementary qualitative analysis.Latimer, George W., Jr. J. Chem. Educ.1967, 44, 537.

Stoichiometry |

Oxidation / Reduction |

Reactions |

Titration / Volumetric Analysis |

Qualitative Analysis

OzonolysisDiaper, D. G. M.Incorrect emphasis in the presentation of the ozonolysis of olefins has caused misconceptions about its scope and utility.Diaper, D. G. M. J. Chem. Educ.1967, 44, 354.

Stereochemical correlations in the camphor seriesMarkgraf, J. HodgeThis paper presents a series of experiments that require the student to interpret the effect of structure on the steric course of an oxidation and a reduction in a bicyclic system.Markgraf, J. Hodge J. Chem. Educ.1967, 44, 36.

Letter to the editorGarrigan, George A.Comments on the teaching potential of an earlier published experiment involving the acid catalyzed hydrolysis of sucrose.Garrigan, George A. J. Chem. Educ.1966, 43, 681.

Carbohydrates |

Mechanisms of Reactions |

Catalysis

Substitution reactions in octahedral complexesJones, G. R. H.Examines the possibility of direct substitution, in aqueous solution, of a ligand in an octahedral complex by a nucleophile other than water or OH-.Jones, G. R. H. J. Chem. Educ.1966, 43, 657.

Coordination Compounds |

Mechanisms of Reactions |

Aqueous Solution Chemistry |

Nucleophilic Substitution |

Transition Elements |

Metals

Fusion reactions under the microscopeBenedetti-Pichler, A. A.; Vikin, JoeAn electrically heated wire is used to identify a variety of cations and anions according to colors observed under a microscope.Benedetti-Pichler, A. A.; Vikin, Joe J. Chem. Educ.1966, 43, 421.

The use of oxidation potentials in inorganic chemistryJolly, William L.This paper attempts to show, using a minimum of thermodynamics, how oxidation potentials can be used to predict the products and driving forces of oxidation-reduction reactions.Jolly, William L. J. Chem. Educ.1966, 43, 198.

Oxidation / Reduction |

Reactions |

Thermodynamics

Aromatic substitutionDuewell, H.Reports on the use of the molecular orbit theory in a qualitative approach to the activation and orientation of substitution in aromatic systems.Duewell, H. J. Chem. Educ.1966, 43, 138.

A simple kinetic investigation of an organic reaction mechanismLandgrebe, John A.This kinetic experiment allows the student to determine what factors affect the rate of a reaction and how this information can be rationalized in terms of a logical sequence of molecular events.Landgrebe, John A. J. Chem. Educ.1964, 41, 567.

The direct esterification of phenolsOffenhauer, Robert D.It is not true that phenols cannot be esterfied by the direct action of an organic acid; includes an experiment demonstrating the fallacy of this common textbook error.Offenhauer, Robert D. J. Chem. Educ.1964, 41, 39.

Phenols |

Esters |

Reactions

Principles of chemical reactionSanderson, R. T.The purpose of this paper is to examine the nature of chemical change in the hope of recognizing and setting forth the basic principles that help us to understand why they occur.Sanderson, R. T. J. Chem. Educ.1964, 41, 13.

Alkali metal-water reactionsMarkowitz, Meyer M.The typical open-air demonstration of sodium reacting with water does not in reality represent the typical reaction of an alkali metal with liquid water; the article goes on to consider other factors that may influence these reactions.Markowitz, Meyer M. J. Chem. Educ.1963, 40, 633.

Friedel-Crafts alkylationMarsi, Kenneth L.; Wilen, Samuel H.Some organic textbooks state that n-alkyl derivatives cannot be synthesized by the Friedel-Crafts reaction, or that they are formed in only minor amounts, though this is not the case.Marsi, Kenneth L.; Wilen, Samuel H. J. Chem. Educ.1963, 40, 214.

Reactions |

Synthesis

The decarboxylation of organic acidMarch, JerrySimple aliphatic acids (except for acetic) do not give good yields of the corresponding alkanes through decarboxylation, although many organic chemistry textbooks cite this as a general method for the preparation of alkanes.March, Jerry J. Chem. Educ.1963, 40, 212.

The reaction of tertiary amines with nitrous acidHein, George E.Examines the history of investigation into the reaction of tertiary amines with nitrous acid as an example of the inherently conservative nature of science and resistance to new concepts.Hein, George E. J. Chem. Educ.1963, 40, 181.

A Diels-Alder reaction experimentSheppard, William J.The original method of Diels and Alder for the reaction of cyclopentadiene with maleic anhydride is modified for use in the elementary organic laboratory.Sheppard, William J. J. Chem. Educ.1963, 40, 40.

Reactions

The formation of acetone from acetatesYoung, Jay A.; Taylor, John K.Suggests some research activities based on an article published previously in the Journal.Young, Jay A.; Taylor, John K. J. Chem. Educ.1962, 39, A962.

A qualitative elemental analysis system correlated with the periodic tableSwift, Ernest H.; Schaefer, William P.This article describes a new system of qualitative analysis developed especially for instructional purposes as a means of teaching descriptive inorganic chemistry and the principles of chemical reactions. Swift, Ernest H.; Schaefer, William P. J. Chem. Educ.1961, 38, 607.

The reactive intermediates of organic chemistryStewart, RossThe purpose of this paper is to outline a logical presentation of the more important reactive intermediates the student is likely to encounter in organic chemistry.Stewart, Ross J. Chem. Educ.1961, 38, 308.

The side-chain halogenation of n-alkyl benzenesGoldwhite, H.A number of textbooks state that in the halogenation of the side-chains of normal alkyl benzenes with elemental halogens there is a strong tendency for halogenation to take place preferentially at the carbon atom next to the aromatic nucleus; the literature does not support this conclusion.Goldwhite, H. J. Chem. Educ.1960, 37, 295.

The principle of minimum bending of orbitalsStewart, George H.; Eyring, HenryThe authors present a theory of valency that accounts for a variety of organic and inorganic structures in a clear and easily understood manner.Stewart, George H.; Eyring, Henry J. Chem. Educ.1958, 35, 550.

Atomic Properties / Structure |

Molecular Properties / Structure |

Elimination Reactions

The reduction of carbon dioxideHollander, Jerome; Spialter, LeonardExamines the reduction of carbon through a variety of processes, including catalytic hydrogenation, reduction by metals and complex metal hydrides, electrochemical reduction, and reduction under the influence of radiation. Hollander, Jerome; Spialter, Leonard J. Chem. Educ.1958, 35, 446.

Spot reaction experiments (Tr. by Ralph E. Oesper)Feigl, FritzThe development of new spot tests for organic analysis led to the discovery of reaction modes of organic compounds, which are of interest as spot tests for teaching purposes.Feigl, Fritz J. Chem. Educ.1957, 34, 457.

Le Châtelier's principle and the equilibrium constantMiller, Arild J.Many students of chemistry have difficulty in understanding how the position of equilibrium in a gaseous reaction can change when the pressure is altered, in accordance with Le Châtelier's principle, without causing a corresponding variation in the equilibrium constant.Miller, Arild J. J. Chem. Educ.1954, 31, 455.

The mechanisms of the reactions of aliphatic hydrocarbonsSchmerling, LouisExamines the formation of carbonium ions and free radicals, the polymerization of olefins, hydrogen-halogen exchange, the condensation of haloalkanes with alkenes, the alkylation of paraffins, the condensation of paraffins with chloroolefins, the cracking of paraffins and olefins, and the isomerization of paraffins.Schmerling, Louis J. Chem. Educ.1951, 28, 562.